The home side will be looking to bounce back from an opening defeat last time out, while the visitors set out to make it back to back wins to kick off their qualifying campaign.
Match preview
Guinea-Bissau saw off the threat of Sao Tome and Principe in an emphatic 5-1 victory in Thursday's clash at the Stade Adrar in Agadir.
Baciro Cande's men went behind in the 21st minute to Edmilson Vegas's opener before strikes from Alfa Semedo, Zidane Banjaqui, Jorginho and Zinho Gano turned the game on its head.
Aiming for a qualify for a fourth straight continental finals, The Djurtus lead the way in Group A of the qualifiers after the first round of matches, albeit only on goal difference.
Coming up next is the challenge of an opposing side who are yet to taste defeat in any of the previous two meetings between the teams which both came back in 2007.
Having recorded clean sheets in three of their last four matches on the road, Monday's visitors will be looking to put on another solid defensive display away from home.
Sierra Leone saw their two-game winning run snapped following a 2-1 loss against Nigeria on Thursday at the Abuja National Stadium.
John Keister's men opened the scoring in the 11th minute through Jonathan Morsay but goals from Alex Iwobi and Victor Osimhen saw them come away empty-handed.
The Leone Stars now set out to get their qualifying journey up and running as they go in search of consecutive AFCON appearances for the first time since 1996.
Still yet to win any of four competitive games since the turn of the year, Monday's hosts will need to get their act together as soon as possible to avoid being left with too much catching up to do.
Sierra Leone Africa Cup of Nations Qualifying form:
Sierra Leone form (all competitions):
Guinea-Bissau Africa Cup of Nations Qualifying form:
Guinea-Bissau form (all competitions):
Team News
Zinho Gano has now found the back of the net three times in his last two games for Guinea-Bissau and the forward is one to keep an eye on.
Having both come off the bench to good effect last time out, Jorginho and Zidane Banjaqui could be rewarded with a place in the starting XI this time around.
Off the back of scoring his first goal for Sierra Leone, Jonathan Morsay will be seeking to pick up where left off versus Nigeria.
Nineteen-year-old Kallum Cesay would have been disappointed not to have featured in the aforementioned game after his brace during the last international break but we expect him to play a part on Monday.
Sierra Leone possible starting lineup:
Kamara; Samadia, Caulker, Sesay, Kakay; Koroma, Kamara, Conteh; Turay, Morsay, Bundu
Guinea-Bissau possible starting lineup:
Gomis; Encada, Mane, Sangante, Cande; Camara, Nogueira, Semedo; Dalcio, Gano, Piqueti